Sitting in the cabin of the boat ten feet off the ground I felt like I was in the belly of a whale, swallowed whole by her size. Her current owner left me instructions to tie up the tarp properly for the impending snow storm and left me to fiddle around unbothered. 
The first time I ever sailed was on a 43-foot catamaran during a 1200 nautical mile trans-Tasman journey. From there I sailed on everything from tall ships to day sailors, with the majority of my time sailing spent aboard a 22-foot pocket cruiser. Ever since that fateful day that I learned about small boats, size has mattered.
I’m not a purist, or a good enough sailor to be considered an authority on anything, but I scoff at fancy boats. Give me something with a simple rig, good bones, an adequate anchoring system and a simple way to charge a handheld VHF.
All signs from my self-survey pointed to this boat being a winner. Yes, there were some signs of delamination on deck but nothing indicated an entirely rotten core. Yes, she had beads of silicone around some fittings that indicated leakage. Yes, some of the bolts on the lifeline stanchions were rusted. Yes, her main sail would need to be retired almost immediately. But none of this seemed beyond my skills or budget for replacement or repair. She even had a working outboard motor and the head had been ripped out years prior (I come from the school of using a bucket as a head, just ask Teresa Carey, so that was a plus for me). The biggest issues I found were rusty chainplates and lack of a working 12 volt electricity system. Both were a turn off, but not enough to pull the plug.
The price was right. The owner was honest. It wasn’t the work that needed to be put in that would swallow me, it was her magnitude. She was closer to it but wasn’t “the one.” Now, I look forward to meeting her little sister. . .
“At sea, I learned how little a person needs, not how much.” – Robin Lee Graham
Am I missing your subscription button?
Seems you’ve found it. Thanks heaps for your continued interest.
it’s so funny to hear you say it’s too big. My dad has a story he likes to tell about going for a sail with my grandpa on his bristol 27 before he married my mom. He always says he felt like he was getting put in a coffin with those quarter berths. maybe this one is laid out differently without an inboard, though?
Oh wait, now that I think of it you were never going to lower the QB’s rather cut out some other part for more comfortable seating. I remember you mentioning that.
Perhaps, this had two settees to port and starboard. Uhm, nothing feels more coffinlike than the quarter berths on fiddlehead 😉 Did you ever wind up dropping them down a few inches? I hope you realize I’m totally joking around and love your boat!!
No quarter berths? Just an aft galley and big cockpit lockers?
What’s under the cockpit if there’s an outboard? Did it have an inboard previously? Is there a prop aperture?
I’m still a novice, so please excuse my somewhat ignorance to these questions. I didn’t realize there was a difference between settee and quarter berth (now I do) and I can’t recall if the berths ran under the cockpit. I looked at my photos and don’t have the right angle to tell exactly but it looks like they don’t. Yes, aft galley and big lockers. No prop aperture to my memory or from my photos of the rudder, etc. But something strange, I found this secret compartment like area in the boat under the sink/ladder into the cabin area that had this weird bell, and when I looked into it (it led back to the cockpit) it was just empty hollowness. I didn’t understand, but maybe there was an inboard in there once.
Nice EH for sale. 6K
http://www.sailboatlistings.com/view/55303
Wow she’s sweet! Going to do some research on these boats, thanks!
Don’t sell yourself short Emily! You know a lot more than you let on. What you’re describing is probably a bad sign for how the owner cared for the vessel. Sounds like he ripped out the inboard, slapped an outboard on the back, but never finished the job. It might not be a bad rig, but if it doesn’t feel right, it’s not the boat for you.
Thanks for the encouragement, Matthew! Yes, it was indeed apparent how he cared for his boat. In fact, he didn’t really care much for her at all. Just let her sit on her mooring every season for daysails here and there. Not much more maintenance was ever done aside from bottom paint. The search continues…
Greetings Emily! My son, who is graduating from high school in May 2016, is searching for a 26-27′ sailboat to take him through the Caribbean. We’re in Charleston, SC and he found a Bristol 27 in Manchester, MA that is posted on SailboatListings.com. The Bristol looks like she may be a good fit, but it’s going to be expensive for him to go see her. I wonder if maybe she’s the same Bristol 27 you saw that looks rather un-cared for? Would greatly appreciate hearing from you either way. Thanks very much! Dean
Sent you an email, Dean! Happy to help. How exciting for your son.
Emily,
The EO at sailboatlistings.com is a good boat. The interior is Hinkley finished, opposed to mine which is vinyl. The sole is teak/holly, mine is white gelcoat. The boat is in excellent condition (from the listing I”m inferring) with new roller furler and 150 headsail, and two new SS jib winches. The brightwork is sparkling and kept up. New cushions, which means a lot since old ones smell and look bad.
The engine needs to be looked at closely but looks ok. The main thing with engines is compression, so if you were to get a survey I would ask for that. It indicates how “tight” your engine is meaning valves and rings are good. Of course there are other things to look at but that is the main measurement.
The big difference between my boat and this one (besides the interior and condition) is mine has the factory bowsprit which allows a cutter rig. This one doesn’t have that but does have the new roller furler and 150 headsail.
Another great thing about this small cruser is the forward cabin. It is a multi-use area with head, huge amounts of storage areas and lockers and a small sink.
It also has a bimini, which is often overlooked but sailing in the sun you need shade. If you are going to meander down the ICW and into FL -> Bahamas a bimini is required.
By the way sailing in the Bahamas is quite straightforward. A bunch of daysail hops will get you down to Turks and Caicos. The first overnight would be to the Dominican Republic if you wanted to get that far. And yes, no sailing at night is the rule.
Anyway I’m still feeling that whatever boat you buy should have all the right stuff including good sail.
Best of luck
Ahoy, thanks for all that input I really appreciate your sound advice! I thought you had a Falmouth Cutter, not an Eastward Ho??